by RandomGuy

Gender: Male
Age: 29
Race/ethnicity: Caucasian
Current location: Los Angeles
Highest education received: College degree (eg., BA, BS)
Occupation: Management
Relationship status: Single
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 16
How many hookup stories have you here posted before? 4

The Other Sister

How long ago did this hookup happen? 9 or so years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Fuck-buddies

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Heather was Asian, 5’5″ or so, slender with 36C’s and a nice tight ass. She had long curly hair that almost went to her butt. I had known her a few years as she was the sister of the girl I had been dating for a while. I was always sexually attracted to her but found her personality a little off-putting.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had been dating her sister for something like a year at this point. They had invited me to a pool party at their parents place so I tagged along. There were quite a few family members there grilling and playing in the pool. My girlfriend Stacey was looking pretty good in her bikini but damn when Heather showed up in hers she was filling it in all the right places. At the time she was engaged to someone but they were often fighting and he wasn’t there this time. At one point Heather was walking around and I found myself checking out her ass. She caught me and I tried to play it off like I was looking elsewhere. At one point later in the day my girlfriend and her parents went to the store for some dessert. I opted to go change out of my swimsuit as the others did as well since it was starting to get cold. I went into my girlfriend’s old room and and began to change. All of sudden there was a knock on the door. I was still clothed so I opened it to see Heather. She asked if she could change in the room as her was being used by her cousin and someone was in the bathroom. I told her I would leave while she changed. She said it was alright to stay as long as I didn’t look. I insisted on leaving but she said she wanted to talk. I reluntantly agreed. Closing the door, she locked it behind her. I stood in a corner and we started talking about her and her fiance and some of their problems. I tried to keep my eyes away as I heard the wet fabric hitting the floor. I really wanted to look but tried to keep my curiosity in check. That’s when I realized that the mirror in front of my gave me a first class view of her bare ass behind me. What’s worse is she was looking over her shoulder and knew I could see. She shook her butt asking if I liked it. I tried to keep things joking by saying it was very nice. She told me she saw me checking her out. I responded with a “well you are pretty attractive.” She turned around giving me a full on view of her naked body and walked over. She wrapped her arms around me grabbing my now rock hard dick and asking if I wanted to have some fun. Of course my body wanted it but I didn’t want to cheat on my girlfriend. But to be fair we hadn’t had sex in almost 4 months since she always would say she wasn’t in the mood. Heather began to rub my cock and whispered that she wouldn’t tell if I didn’t. I am sad to say I gave in.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? Heather peeled my swim trunks down revealing my throbbing erection. She got on her knees and began to suck me off. She made a comment about the chlorine but kept going. After a few minutes she stopped and got up. She walked over to Stacey’s bed and laid down with her ass up doggy style. She said sexually, “Fuck me on my sister’s bed.” It kinda hit me in the gut when she said that but as she wagged her ass, I relented. I walked over and shoved my dick into her tight, bare, Asian pussy. I had done it – I had cheated on my girlfriend, and, of all people, with her sister on her bed. As I pounded away we both kept as quiet as possible. It wasn’t long before I got close. I asked if I should pull out. She said no as she was on the pill. I ended up cumming, dumping a huge load into her pussy. She moaned quietly as I did.

Did you have an orgasm? Did your partner(s)? I came but she didn’t

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No condoms or prior talk about STI. She was on the pill.

What were your REASONS for having this hookup? Lust, plain and simple

Were alcohol or drugs involved? If so, how much? None

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? After I came she kissed me deeply and asked if I enjoyed it. I said yes and she smiled, putting her clothes on. She left, making sure no one saw. I got dressed, feeling guilty about it. When my girlfriend and parents came back we ate dessert at the table. I had a hard time looking at Stacey, having done what I just did. While at the table I got a text from Heather saying she could feel my cum dripping from her pussy. Afterwards Heather asked to meet again. I told her that I still had affections for Stacey. She said she still loved her fiancé but she liked the idea of having a fuck buddy on the side. I was hesitant at first but she would send me suggestive photos and told me that as fuck buddies we could fulfill our fantasies together. We ended up meeting and fucking dozens of times. She was the first time I ever fucked a girl in the ass and my first time fucking someone in public. We did a lot of things that a normal couple wouldn’t never do. As time went on Stacey and I broke up, it was mutual as it seemed we just didn’t have the same paths in life. Heather ended up marrying her fiancé and wanted to keep meeting with me but I told her that I didn’t want to risk her marriage. We met one more time after that but only as friends.

To whom did you talk about the hookup? How did they react? We both kept it pretty quiet. Though I later found out she had secretly recorded some of our sex sessions for her own personal pleasure. She ended up showing her best friend whom ended up having sex with her afterwards. She recorded that as well and had sent it to me offering me a threesome.

Was this a consensual and/or wanted experience for you? For your partner? Yes

Do you regret this hookup? If so, why? I did and still do a little, but at the time sex was off the plate in my relationship so like a person who fell off a boat into an ocean I grabbed whatever I could to stay afloat.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Getting to have no strings attached carnal sex with a beautiful Asian woman was amazing. Having a double affair bothered me quite a bit.

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? Somewhat negative

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